nitric acid; NH4VO3 in water T=55 - 60°C; 5 h;

1: 68 percent / TiCl4, N-methylmorpholine / tetrahydrofuran; CCl4 / 22 h / 0 °C 2: 73 percent / H2 / PtO2 / ethanol / 7 h / 100 °C / 76000 Torr 3: 57 percent / NaH / dioxane / 1.) r.t., 4 h, 2.) reflux, 2 h 4: 69 percent / conc. HCl / 24 h / Heating View Scheme

1: toluene / Rosemund reduction 2: 68 percent / TiCl4, N-methylmorpholine / tetrahydrofuran; CCl4 / 22 h / 0 °C 3: 73 percent / H2 / PtO2 / ethanol / 7 h / 100 °C / 76000 Torr 4: 57 percent / NaH / dioxane / 1.) r.t., 4 h, 2.) reflux, 2 h 5: 69 percent / conc. HCl / 24 h / Heating View Scheme

1: SOCl2 2: toluene / Rosemund reduction 3: 68 percent / TiCl4, N-methylmorpholine / tetrahydrofuran; CCl4 / 22 h / 0 °C 4: 73 percent / H2 / PtO2 / ethanol / 7 h / 100 °C / 76000 Torr 5: 57 percent / NaH / dioxane / 1.) r.t., 4 h, 2.) reflux, 2 h 6: 69 percent / conc. HCl / 24 h / Heating View Scheme

1: 73 percent / H2 / PtO2 / ethanol / 7 h / 100 °C / 76000 Torr 2: 57 percent / NaH / dioxane / 1.) r.t., 4 h, 2.) reflux, 2 h 3: 69 percent / conc. HCl / 24 h / Heating View Scheme

hydrogenchloride 24 h; Heating;

1: 57 percent / NaH / dioxane / 1.) r.t., 4 h, 2.) reflux, 2 h 2: 69 percent / conc. HCl / 24 h / Heating View Scheme